


Strive to Find the Heavens

by waitingforjudas



Series: Judas' Kinktober 2019 [19]
Category: Teen Wolf (TV)
Genre: Double Penetration, Double Penetration in One Hole, Established Derek Hale/Stiles Stilinski, Kinktober, Kinktober 2019, M/M, Marijuana, Mildly Dubious Consent, Minor Vernon Boyd/Erica Reyes, Other: See Story Notes, Shotgunning, it's just mentioned
Language: English
Status: Completed
Published: 2019-10-20
Updated: 2019-10-20
Packaged: 2020-12-24 14:55:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,403
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21101333
Author URL: https://archiveofourown.org/users/waitingforjudas/pseuds/waitingforjudas
Summary: Derek’s had a fantasy for years, but it’s hard to get one dick in his hole on a good day. Stiles makes a suggestion to help him relax.Written for Kinktober 2019 prompts: Shotgunning and Double Penetration.





	Strive to Find the Heavens

**Author's Note:**

> This is 10/19’s short. Working on 10/18’s. 
> 
> 10/20 will be Destiel, as will 10/22, 10/23, 10/24, and 10/28. A couple other days are still unplanned/undecided. 
> 
> For more information on the dubious consent (contains spoilers), see the end notes. 
> 
> _Written for Kinktober 2019. Prompt list can be found at https://twitter.com/NihilistShiro/status/1162794889970511872._

“Your biggest fantasy,” Stiles said, and took another hit, breathing the weed in deep. 

It tickled Derek’s nose, and he fought back a sneeze. “Two cocks.”

Stiles laughed. “Me, too. Oh, my god, think of how epic that’d be, two penises instead of one. Although—I mean, jerking it would get a little weird. How would I—”

“No, I mean.” Derek blushed. “Two cocks. Two people. Inside of me.”

“Oh.” Stiles’ eyebrows shot to his hairline. “Really? You’re not that into penetration most of the time.”

Derek shrugged, looking down at his fingernails and extending a claw to scratch out flecks of dirt. “It can… hurt. I get too tense, and the healing just… works from there, I guess.”

Stiles hummed, but he leaned back. 

“What are you thinking?”

Stiles glanced at him. “Well. Weed works on you, right?”

“It… relaxes me. I don’t hallucinate.”

“Just a thought, but… what if you smoked it? I mean, we could call someone—assuming you have someone in mind—and see if they’re willing to do it. You’d be relaxed enough.”

Derek blinked. “Why didn’t I think of that before?” 

Stiles shrugged, grinning lazily. “This is why you need me, Der. I’m fucking awesome. Who did you have in mind? I know it’s somebody, not a dildo. I won’t be jealous, I swear.”

Derek blushed, pulling a knee up to his chest. “Maybe….”

###

“Hi, Boyd!” Stiles said, grinning. 

Derek offered a—shaky—hand, which Boyd took easily. 

“Good to see you, Derek,” Boyd said. 

“Erica was seriously okay with this?” Stiles asked, rolling another joint. 

“Assuming I don’t drive for a few hours after this.” Boyd shrugged. “And assuming I tell her whether Derek has a ‘bubble butt.’ I hope you know what that means.”

“Don’t front,” Stiles said. “Everybody knows his ass is all that.” Stiles slapped said ass with a free hand and Derek blushed further. 

He hadn’t stopped blushing since he’d told Stiles he thought Boyd would be the best choice—the most reasonable, anyway. Boyd wouldn’t laugh him out of the room, and if Derek couldn’t go through with it, Boyd wouldn’t mind. 

“Okay,” Stiles said, “let’s get this party rockin’. Derek, you high enough?”

“Were you high when you decided to do this?” Boyd asked. 

“A little,” Derek said. “Just secondhand.”

“But _now_ he’s gonna get high so he can relax. I’m assuming your dick lives up to Erica’s hype, and while I know Derek doesn’t hype me up, I’m not _tiny_.”

Boyd had a shadow of a smile on his face. “I’d take Erica’s measurements with a grain of salt.” 

Stiles nodded sagely, then froze. “Wait, which _way_? Are you _bigger_?”

Derek groaned. “Stiles, do you see how that’s not very efficient?”

“Or effective,” Boyd said. 

“Yup, nope, got it, let’s fuck Derek’s tight little ass open. Go, team!” Stiles pulled out his lighter and led the way to the bedroom. 

“You can always back out,” Derek whispered. 

“Same goes for you.”

Derek nodded. His palms were sweating. 

Stiles had lit the joint but was just holding it in his mouth as he stripped out of his pants. “Okay, _your_ turn.” He pointed to Derek. “Show Boyd that bubble butt. God, Erica would never let me hear the end of it if you tell her Derek’s ass _isn’t_ all that.”

Derek snorted, as did Boyd. 

“She’ll never let you hear the end of it either way,” Boyd said, offering a hand for Derek to hold on to for support like it was instinct. It damn well could’ve been, too. 

Derek stepped out of his sweatpants. His cock was heavy underneath his boxer briefs and Stiles waved a hand at him. “Off already.”

Derek flushed, glancing to Boyd. “Last chance.”

“I’m in if you are,” Boyd said. His gaze was—strangely enough—rather lust-filled. 

Derek shoved his underwear down. 

Stiles wolf-whistled, and Boyd made a—much more muted—appreciative noise. 

“Hands and knees, on the bed,” Stiles said, and took a drag of smoke. 

Derek obeyed, climbing up, trying not to tense up at how exposed he was already. Stiles leaned in and pressed his lips to Derek’s, but when Derek opened his mouth, he blew smoke into Derek’s mouth instead. 

Derek coughed a little, but tried to inhale it all. The effect was almost instantaneous—he could feel his muscles loosening, including his hole. 

“Lube?” Boyd asked, and Derek could hear fabric shifting on skin. 

“Top drawer.” Stiles blew another breath into Derek’s mouth and Derek felt himself growing almost—floppy probably wasn’t the right way to put it, but that’s how it felt. Loose, wobbly—floppy. 

Warm, slick fingers touched his hole and Derek moaned, not even thinking to stifle the noise. 

“Isn’t he responsive?” Stiles said and shotgunned one last hit to Derek before he walked around the bed and stood with Boyd. “Pretty little hole.”

Boyd grunted. “How much prep?”

“Normally? Half an hour, minimum. Slow. Right now? You’ve already got two. I think you could go for three.” 

Derek felt almost dizzy. He had his best friend’s and his mate’s fingers inside of his ass, and it had only been a few minutes since they started. 

Derek was _floating_, fucking himself back on their fingers as they rubbed at his prostate, slicked over his walls, curled and tightened and suddenly stopped and then brought in more slickness, colder, and—

“He’s ready for at least one,” Stiles was saying. 

Derek nodded, humming. 

The mattress shifted behind him, probably with someone climbing on the bed. 

Derek’s hole tensed despite himself and he whined. The fingers that had just been bringing him so much pleasure were too much, and—

“Shh,” Stiles whispered, and sucked in a breath of marijuana to pass to Derek. 

Derek blew it out through his nose and kissed Stiles, licking into his mouth, tasting the thick, heavy smoke that had flavored his tongue, the roof of his mouth, his _teeth_. 

“Go ahead,” Stiles said. He offered another hit to Derek and Derek sealed his lips onto Stiles’ as his hole relaxed again and then—oh, the fingers left. 

Derek was almost sad, but then something thick and warm and _hard_ was butting up against his hole and he smiled. “More,” he moaned, his smile growing. It felt so good, being filled up without the pain. 

The cock pushed its way inside until the owner’s hips were against his ass, balls against Derek’s perineum. 

“Stiles,” Derek said, and moaned as whoever it was—_Boyd_, Derek was almost certain, but he was dizzy with feeling—rocked in and out, slow and small. “Fuck me. Fuck me, too.”

Stiles nodded eagerly. “More first, okay?” 

Stiles blew smoke into Derek’s lungs a half a dozen more times before Boyd was satisfied with how loose Derek’s hole was. 

“It’s safe,” Boyd said. “Don’t stub it out yet.”

“Wasn’t planning on it,” Stiles said, and then—

_Oh, yes_. 

Stiles’ cock, _his mate’s cock_, was filling him again, and Derek came, spilling his orgasm onto the sheets. 

Stiles leaned down a moment later and Derek sucked in the weed without hesitation, all in one big gasp, and groaned it out as his hole loosened further. 

Stiles seated himself back inside and Derek was snug enough again, and then he just—he just held himself up, waiting for Boyd and Stiles to finish, to shoot deep in his ass and fill him with their come. 

Boyd came first, claws scratching into Derek’s flesh, and Derek moaned along with him. He pulled out and knee-walked around to Derek’s head, where Derek didn’t even think, just sucked his best friend’s cock into his mouth and cleaned him off eagerly. 

“God— Shit, _Derek_— Good boy,” Stiles said, and Derek sucked harder on Boyd’s cock. 

Stiles shot inside of him a moment later and kept fucking through his orgasm before collapsing on top of Derek’s back heavily. 

Derek wiggled his hips a little, trying to encourage Stiles to get up and let him clean off his cock, too. 

Stiles got the hint quick enough and Boyd pulled away to let Stiles have his turn. 

“Any plans for a repeat?” Boyd asked a few minutes later. 

Derek let go of Stiles’ cock. “Please.” 

Stiles fed his cock back into Derek’s mouth. “You’re gonna finish blowing me first.” 

Derek bobbed his head, working Stiles’ cock down his throat. 

Round two would be even better—Derek was sure of it.

**Author's Note:**

> If you enjoyed, please consider leaving kudos or a comment. 
> 
> The dubious consent is because Stiles and Derek get the idea to have sex while already high, and this could be interpreted as coercion on Stiles' part. Derek also smokes throughout the sex, and his capacity is noted to be lessened and the ability for him to revoke consent is somewhat diminished. 
> 
> _This work was inspired by @NihilistShiro's Kinktober prompt list, available here: https://twitter.com/NihilistShiro/status/1162794889970511872 _


End file.
